Alkylation of Cyclic Ketones and Related Compounds

The first example of the use of an alkaloid-based chiral phase-transfer catalyst as an efficient organocatalyst for enantioselective alkylation reactions was reported in 1984 [3, 4]. Researchers from Merck used a cinchoninium bromide, 8, as a catalyst 

Asymmetric Organocatalysis. Albrecht Berkessel and Harald Groger Copyright 2005 WILEY-VCH Veriag GmbH Co. KGaA, Weinheim ISBN 3-527-30517-3 

The broad substrate range, in particular with regard to the alkyl halide component, led to numerous interesting applications of this asymmetric phase-transfer-catalyzed alkylation using alkaloids as catalyst [6-18], Selected examples are described below. 

Derivatives of commercially available alkaloids, e.g. 8 and 13, have usually been used as the phase-transfer catalyst. Besides these classic standard catalysts, however, efforts have been also made to design novel organocatalysts with new proper- 

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